Confessions of a globe-hopping, adrenaline-seeking venture capitalist
CBS didn’t just cancel The Late Show with Stephen Colbert. They shuttered a format that for decades defined cultural prime time because the economics stopped working. In 2020, Colbert’s show employed 200 people, cost roughly $100M a year to produce, and brought in $120M; a modest $20M profit. By 2024, revenue had been cut in [ ]
Over the last decade, emerging markets have become a magnet for global venture capital. The pitch is compelling: leapfrog technologies, vast unbanked populations, mobile-first users, minimal legacy technical debt (i.e., no entrenched systems to unwind), and digital tailwinds tied to GDP growth. From Nairobi to São Paulo to Ho Chi Minh City, global investors are [ ]
Venture investors often covet board seats. They’re seen as strategic assets: sources of leverage, control, and relevance. But the reality is more complicated. In many cases, board seats quietly erode investor time, flexibility, and focus — without materially improving outcomes for founders or funds. The most expensive asset in venture capital isn’t dilution. It’s time [ ]
Dating apps are stalling. Social media feels stale. The next wave of consumer social may not be more deliberate than digital. (I covered some of this in my recent post, ‘Dating Apps Are Collapsing: What It Says About Changing Consumer Behavior.’ ) Here’s why offline is quietly becoming the new premium layer. 1. Consumer Social [ ]
In the current wave of AI innovation, one term has become especially fashionable: infrastructure. Founders use it as a shorthand for defensibility, scale, and category leadership. Investors often hear it and lean in reflexively, hoping to spot the next Snowflake, Hugging Face, or Databricks. But lately, there’s a widening gap between what founders call infrastructure [ ]
In a matter of weeks, OpenAI’s $3 billion bid for Windsurf collapsed. Within days, Google stepped in — not with an acquisition, but with a $2.4 billion licensing and compensation package that brought Windsurf’s leadership and key technical staff into DeepMind. The legal entity remains. The team does not. Meanwhile, Meta’s $15 billion investment for [ ]
The startup world prides itself on velocity, vision, and disruption. But underneath the surface — between funding rounds and product milestones — many high-growth environments quietly accumulate organizational debt. And when that debt compounds, it doesn’t show up on the balance sheet. It shows up in the form of toxic workplaces, ineffective managers, and high [ ]
Bumble is laying off 30% of its workforce. Tinder, once a category-defining juggernaut, has shed more than 80% of its market capitalization since its peak. These aren’t isolated signals. They’re data points in a larger story — one that has less to do with dating, and more to do with shifting consumer behavior, cultural fatigue, [ ]
Media critics have long accused broadcast and cable TV networks of being stuck in a 1980s business model, unwilling to adapt for fear of cannibalizing their cushy franchises. The surge in streaming is forcing change In May 2025, the inevitable became official. According to Nielsen’s The Gauge, streaming captured 44.8% of total television viewing — [ ]
For much of the past decade, venture capital rewarded breadth over depth. In a capital-abundant environment, venture investors that lacked technical expertise, operating skills or much in the way of differentiation were able to thrive. They moved fluidly across sectors and geographies, leaned on pattern recognition over domain fluency, and often secured allocations in competitive [ ]